Efficient enantioselective synthesis of functionalized tetrahydropyrans by Ru-catalyzed asymmetric ring-opening metathesis/cross-metathesis (AROM/CM)

DG Gillingham, O Kataoka, SB Garber…

Index: Van Veldhuizen, Joshua J.; Gillingham, Dennis G.; Garber, Steven B.; Kataoka, Osamu; Hoveyda, Amir H. Journal of the American Chemical Society, 2003 , vol. 125, # 41 p. 12502 - 12508

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Citation Number: 124

Abstract

An efficient method for enantioselective synthesis of highly functionalized pyrans (up to 98% ee) through Ru-catalyzed asymmetric ring-opening metathesis/cross-metathesis is described. Reactions are promoted by a recyclable chiral Ru-chloride or a new chiral Ru- iodide complex; the latter catalyst is less efficient but gives rise to significantly higher levels of enantioselectivity. Catalytic reactions can be performed in undistilled solvent and with a ...